||A short synthesis of (+)-β-lycorane by asymmetric conjugate addition cascade
Nishimura, Katsumi ,
Fukuyama, Naoshi ,
Yasuhara, Tomohisa ,
Yamashita, Mitsuaki ,
Sumiyoshi, Takaaki ,
Yamamoto, Yasutomo ,
Yamada, Ken-ichiTomioka, Kiyoshi
7226 , 2015-09-30 , Elsevier Ltd.
The chiral diether ligand-controlled asymmetric conjugate addition of organolithiums to nona-2, 7-dienedioate and subsequent intramolecular conjugate addition of the enolate intermediate gave all-trans trisubstituted cyclohexanes with high ee and yields. Using this methodology, an efficient short asymmetric total synthesis of (+)-β-lycorane was accomplished in 33% overall yield through five steps from the dienedioate.